Drake may seem like an unlikely Meek supporter, but the two have history together. Before becoming rivals with “Back to Back,” “Charged Up,” and “I Wanna Know,” they were associates and collaborators on “Amen” and “R.I.C.O.”

The OVO boss has famously worn the “Free Meek Mill” shirt himself, on multiple occasions. In 2014, he sported it on tour, showing support for the rapper, who had been incarcerated.

But in 2015, he wore it more ironically. After beefing with Meek over ghostwriting allegations, Drake prepared for OVO Fest in a “Free Meek Mill” shirt.

Drake is the latest artist to voice support for Mill, who was recently sentenced to 2-4 years in prison for probation violations. JAY-Z, Rick Ross, Wale, T.I., and other rappers have also spoken on Mill’s behalf, saying that the sentence was harsh.

Over the weekend, the Philadelphia rapper was transferred out of solitary confinement to the State Correctional Institution in Chester, Pennsylvania, where is now in general population. His legal team is now fighting the case, claiming that the judge’s conduct has been inappropriate.